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Short electrochemical asymmetric synthesis of (+)-N-acetylcolchinol

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posted on 2022-10-07, 13:13 authored by Yi Du, Adelaide Lunga, Aleksandr Rubtsov, Andrei MalkovAndrei Malkov

A short synthesis of N-acetylcolchinol using a greener and step-economical pathway is reported where all the redox reactions, except for the asymmetric reduction, were carried out electrochemically, replacing protocols that employ transition metals or toxic reagents. In a 4-step racemic sequence, chemoselective reduction of chalcone and intramolecular oxidative arene-arene coupling were performed in an electrochemical cell giving the target N-acetylcolchinol with an overall 41% yield. In a 7-step asymmetric variant, electrochemistry was also employed for the deprotection of p-methoxyphenyl amine. The target compound was obtained with a 33% overall yield and 99.5:0.5% er. 

Funding

BENIGN CASCADE EXTRACTIVE BIOREFINERY FOR CONVERTING AGRI-FOOD SIDE STREAMS INTO HIGH-VALUE POLYPHENOLIC BIOACTIVES AND FUNCTIONAL FIBRES FOR PHARMA, COSMECEUTICALS, NUTRACEUTICALS AND FOOD PRODUCTS

European Commission

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Loughborough University

History

School

  • Science

Department

  • Chemistry

Published in

Green Chemistry

Volume

24

Issue

18

Pages

7220-7226

Publisher

Royal Society of Chemistry

Version

  • VoR (Version of Record)

Rights holder

© The Authors

Publisher statement

This is an Open Access Article. It is published by the Royal Society of Chemistry under the Creative Commons Attribution-NonCommercial 3.0 Unported Licence (CC BY-NC). Full details of this licence are available at: https://creativecommons.org/licenses/by-nc/3.0/

Acceptance date

2022-08-25

Publication date

2022-09-01

Copyright date

2022

ISSN

1463-9262

eISSN

1463-9270

Language

  • en

Depositor

Prof Andrei Malkov. Deposit date: 1 September 2022

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